| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 4/5 | 3:45 PM | Varsity | League | Normal | Home | East Lyme | Loss | 3-4 | | Ledyard High School - Tennis Courts | |
| TUE 4/16 | 3:45 PM | Varsity | League | Normal | Home | Fitch | Loss | 1-6 | | Ledyard High School - Tennis Courts | |
| MON 4/22 | 3:45 PM | Varsity | League | Normal | Away | East Lyme | Loss | 1-6 | | East Lyme High School - Tennis Courts | 2:30 PM - 1 Bus |
| TUE 4/23 | 3:45 PM | Varsity | League | Normal | Away | Killingly | Win | 5-2 | | Killingly High School - Tennis Courts | 2:30 PM - 1 Bus |
| WED 4/24 | 4:00 PM | Varsity | League | Normal | Home | Woodstock Academy | Win | 6-1 | | Ledyard High School - Tennis Courts | |
| FRI 4/26 | 3:45 PM | Varsity | League | Normal | Home | Norwich Free Academy | Win | 7-0 | | Ledyard High School - Tennis Courts | |
| MON 4/29 | 3:45 PM | Varsity | League | Normal | Home | Killingly | Win | 7-0 | | Ledyard High School - Tennis Courts | |
| THU 5/2 | 3:45 PM | Varsity | League | Normal | Home | Montville | Win | 6-1 | | Ledyard High School - Tennis Courts | |
| FRI 5/3 | 4:00 PM | Varsity | League | Normal | Away | Lyman Memorial | Win | 6-1 | | Lyman Memorial High School - Tennis Courts | 2:30 PM - 1 Bus |
| TUE 5/7 | 3:45 PM | Varsity | League | Normal | Home | Stonington | Loss | 1-6 | | Ledyard High School - Tennis Courts | |
| WED 5/8 | 3:45 PM | Varsity | League | Normal | Away | Norwich Free Academy | Win | 7-0 | | Rec Fields - Armstrong Tennis Courts | 2:30 PM - 1 Bus |
| FRI 5/10 | 3:45 PM | Varsity | League | Normal | Home | New London | Win | 6-1 | | Ledyard High School - Tennis Courts | |
| MON 5/13 | 3:45 PM | Varsity | League | Normal | Away | Waterford | Loss | 2-5 | | Waterford High School - Tennis Courts - WHS | 2:30 PM - 1 Bus |
| TUE 5/14 | 6:15 PM | Varsity | League | Normal | Away | Woodstock Academy | Win | 4-3 | | Pomfret School - Field House | 4:15 PM - 1 Bus |
| MON 5/20 | 3:00 PM | Varsity | Postseason | Normal | Away | | | | | Stonington High School - SHS Tennis Courts | |
| East Lyme | | |
| Fitch | | |
| Killingly | | |
| Lyman Memorial | | |
| Montville | | |
| Norwich Free Academy | | |
| St. Bernard | | |
| Stonington | | |
| Waterford | | |
| Windham / Windham Tech | | |
| Woodstock Academy | | |
| TUE 5/21 | 3:00 PM | Varsity | Postseason | Normal | Away | | | | | Stonington High School - SHS Tennis Courts | |
| | |
| East Lyme | | |
| Fitch | | |
| Lyman Memorial | | |
| Montville | | |
| Norwich Free Academy | | |
| St. Bernard | | |
| Stonington | | |
| Waterford | | |
| Windham / Windham Tech | | |
| Woodstock Academy | | |
| WED 5/22 | 3:00 PM | Varsity | Postseason | Normal | Away | | | | | Stonington High School - SHS Tennis Courts | |
| | |
| East Lyme | | |
| Fitch | | |
| Lyman Memorial | | |
| Montville | | |
| Norwich Free Academy | | |
| St. Bernard | | |
| Stonington | | |
| Waterford | | |
| Windham / Windham Tech | | |
| Woodstock Academy | | |
| FRI 5/24 | 2:30 PM | Varsity | Postseason | Normal | Home | Seymour | Win | 5-2 | | Ledyard High School - Tennis Courts | |
| SAT 5/25 | 12:30 PM | Varsity | Postseason | Normal | Away | Weston | Loss | 0-7 | | Weston High School - WHS Tennis Courts | 9:15 AM - 1 Bus |